A Molecular Electron Density Theory Study of the [3+2] Cycloaddition Reaction of Pseudo(mono)radical Azomethine Ylides with Phenyl Vinyl Sulphone

References (65)

1. 1 Carruthers, W. (1978). Some Modern Methods of Organic Synthesis, Cambridge University Press. [2nd ed.].
2. 2 Padwa, A. (1984). 1,3-Dipolar Cycloaddition Chemistry, Wiley-Interscience.
3. 3 Carruthers, W. (1990). Cycloaddition Reactions in Organic Synthesis, Pergamon.
4. 4 Padwa, A., and Pearson, W.H. (2002). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, John Wiley & Sons, Inc. [DOI]
5. 5 Domingo, 2010, Understanding the High Reactivity of the Azomethine Ylides in [3+2] Cycloaddition Reactions [DOI]
6. 6 Domingo, L.R., and Ríos-Gutiérrez, M. (2017). A Molecular Electron Density Theory Study of the Reactivity of Azomethine Imine in [3+2] Cycloaddition Reactions. Molecules, 22. [DOI]
7. 7 Domingo, 2018, A Molecular Electron Density Theory Study of the Reactivity and Selectivities in [3+2] Cycloaddition Reactions of C,N-Dialkyl Nitrones with Ethylene Derivatives [DOI]
8. 8 Domingo, 2016, An MEDT study of the carbenoid-type [3+2] cycloaddition reactions of nitrile ylides with electron-deficient chiral oxazolidinones [DOI]
9. 9 Domingo, L.R. (2016). Molecular Electron Density Theory: A Modern View of Reactivity in Organic Chemistry. Molecules, 21. [DOI]
10. 10 Domingo, 2019, Unravelling the Mysteries of the [3+2] Cycloaddition Reactions [DOI]
11. 11 Bailly, 2004, Lamellarins, from A to Z: A family of anticancer marine pyrrole alkaloids [DOI]
12. 12 Bellina, 2006, Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [DOI]
13. 13 Narayan, 2014, Catalytic Enantioselective 1,3-Dipolar Cycloadditions of Azomethine Ylides for Biology-Oriented Synthesis [DOI]
14. 14 Barakat, A., Islam, M.S., Ali, M., Al-Majid, A.M., Alshahrani, S., Alamary, A.S., Yousuf, S., and Choudhary, M.I. (2021). Regio- and Stereoselective Synthesis of a New Series of Spirooxindole Pyrrolidine Grafted Thiochromene Scaffolds as Potential Anticancer Agents. Symmetry, 13. [DOI]
15. 15 Boudriga, S., Haddad, S., Murugaiyah, V., Askri, M., Knorr, M., Strohmann, C., and Golz, C. (2020). Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity. Molecules, 25. [DOI]
16. 16 Barakat, A., Soliman, S.M., Alshahrani, S., Islam, M.S., Ali, M., Al-Majid, A.M., and Yousuf, S. (2020). Synthesis, X-ray Single Crystal, Conformational Analysis and Cholinesterase Inhibitory Activity of a New Spiropyrrolidine Scaffold Tethered Benzo [b] Thiophene Analogue. Crystals, 10. [DOI]
17. 17 Barakat, A., Alshahrani, S., Al-Majid, A.M., Ali, M., Altowyan, M.S., Islam, M.S., Alamary, A.S., Ashraf, S., and Ul-Haq, Z. (2020). Synthesis of a New Class of Spirooxindole–Benzo [b] Thiophene-Based Molecules as Acetylcholinesterase Inhibitors. Molecules, 25. [DOI]
18. 18 Barakat, 2021, Drug Repurposing of Lactoferrin Combination in a Nanodrug Delivery System to Combat Severe Acute Respiratory Syndrome Coronavirus-2 Infection
19. 19 Domingo, 2011, Understanding the Electronic Reorganization along the Nonpolar [3+2] Cycloaddition Reactions of Carbonyl Ylides [DOI]
20. 20 Domingo, 2018, A Molecular Electron Density Theory Study of the Role of the Copper Metalation of Azomethine Ylides in [3+2] Cycloaddition Reactions [DOI]
21. 21 Domingo, 2015, A mechanistic study of the participation of azomethine ylides and carbonyl ylides in [3+2] cycloaddition reactions [DOI]
22. 22 Aziz, 2021, Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation [DOI]
23. 23 Islam, 2021, Synthesis of Spirooxindole Analogs Tethered Pyrazole Scaffold as Acetylcholinesterase Inhibitors
24. 24 Barakat, A., Haukka, M., Soliman, S.M., Ali, M., Al-Majid, A.M., El-Faham, A., and Domingo, L.R. (2021). Straightforward Regio- and Diastereoselective Synthesis, Molecular Structure, Intermolecular Interactions and Mechanistic Study of Spirooxindole-Engrafted Rhodanine Analogs. Molecules, 26. [DOI]
25. 25 Al-Majid, A.M., Soliman, S.M., Haukka, M., Ali, M., Islam, M.S., Shaik, M.R., and Barakat, A. (2020). Design, Construction, and Characterization of a New Regioisomer and Diastereomer Material Based on the Spirooxindole Scaffold Incorporating a Sulphone Function. Symmetry, 12. [DOI]
26. 26 Chai, 2008, Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections [DOI]
27. 27 Hehre, M.J., Radom, L., Schleyer, P.V.R., and Pople, J. (1986). Ab initio Molecular Orbital Theory, Wiley.
28. 28 Schlegel, 1982, Optimization of equilibrium geometries and transition structures [DOI]
29. 29 Yarkony, D.R. (1994). Modern Electronic Structure Theory, World Scientific Publishing. [DOI]
30. 30 Fukui, 1970, Formulation of the reaction coordinate [DOI]
31. 31 Schlegel, 1990, Reaction path following in mass-weighted internal coordinates [DOI]
32. 32 Schlegel, 1991, Improved algorithms for reaction path following: Higher-order implicit algorithms [DOI]
33. 33 Tomasi, 1994, Molecular interactions in solution: And overview of methods based on continuous distributions of the solvent [DOI]
34. 34 Simkin, B.Y., and Sheikhet, I.I. (1995). Quantum Chemical and Statistical Theory of Solutions–Computational Approach, Ellis Horwood.
35. 35 Cossi, 1996, Ab initio study of solvated molecules: A new implementation of the polarizable continuum model [DOI]
36. 36 Cances, 1997, A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics [DOI]
37. 37 Barone, 1998, Geometry optimization of molecular structures in solution by the polarizable continuum model [DOI]
38. 38 Domingo, 2014, A new C–C bond formation model based on the quantum chemical topology of electron density [DOI]
39. 39 Reed, 1985, Natural population analysis [DOI]
40. 40 Reed, 1988, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint [DOI]
41. 41 Parr, R.G., and Yang, W. (1989). Density Functional Theory of Atoms and Molecules, Oxford University Press.
42. 42 Domingo, L.R., Ríos-Gutiérrez, M., and Pérez, P. (2016). Applications of the conceptual density functional indices to organic chemistry reactivity. Molecules, 21. [DOI]
43. 43 Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (Gaussian 16, 2016). Gaussian 16, Revision A.03.
44. 44 Becke, 1990, A simple measure of electron localization in atomic and molecular-systems [DOI]
45. 45 Noury, 1999, Computational tools for the electron localization function topological analysis [DOI]
46. 46 Dennington, R., Keith, T.A., and Millam, J.M. (2016). GaussView, Semichem Inc.. [6th ed.].
47. 47 Johnson, 2010, Revealing Noncovalent Interactions [DOI]
48. 48 Johnson, 2011, NCIPLOT: A Program for Plotting Noncovalent Interaction Regions [DOI]
49. 49 Silvi, 1994, Classification of chemical bonds based on topological analysis of electron localization functions [DOI]
50. 50 Parr, 1983, Absolute hardness: Companion parameter to absolute electronegativity [DOI]
51. 51 Domingo, 2020, A Molecular Electron Density Theory Study of the Reactivity of Tetrazines in Aza- Diels-Alder Reactions [DOI]
52. 52 Parr, 1999, Electrophilicity index [DOI]
53. 53 Domingo, 2008, Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study [DOI]
54. 54 Chamorro, 2020, A Close Look to the Oxaphosphetane Formation along the Wittig Reaction: A [2 + 2] Cycloaddition? [DOI]
55. 55 Aurell, 2004, A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes [DOI]
56. 56 Domingo, 2013, Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions [DOI]
57. 57 Domingo, 2012, Understanding the Origin of the Asynchronicity in Bond-Formation in Polar Cycloaddition Reactions. A DFT Study of the 1,3-Dipolar Cycloaddition Reaction of Carbonyl Ylides with 1,2-Benzoquinones [DOI]
58. 58 Benchouk, 2011, Understanding the kinetic solvent effects on the 1,3-dipolar cycloaddition of benzonitrile N-oxide: A DFT study [DOI]
59. 59 Evans, 1935, Some applications of the transition state method to the calculation of reaction velocities, especially in solution [DOI]
60. 60 Krokidis, 1997, Characterization of Elementary Chemical Processes by Catastrophe Theory [DOI]
61. 61 Domingo, 2008, Understanding the Participation of Quadricyclane as Nucleophile in Polar Cycloadditions toward Electrophilic Molecules [DOI]
62. 62 Fukui, K. (1964). Molecular Orbitals in Chemistry, Physics, and Biology, Academic Press.
63. 63 Gleiter, 1983, Regio- and Stereoselectivity in Diels-Alder Reactions. Theoretical Considerations [DOI]
64. 64 Svatunek, 2021, Origins of Endo Selectivity in Diels–Alder Reactions of Cyclic Allene Dienophiles [DOI]
65. 65 Mayoral, 2000, Do Secondary Orbital Interactions Really Exist? [DOI]

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